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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

1. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is €429
includes taxes & fees
20 Sept - 21 Sept
Fire Pit & Yard: Updated Winter Garden Home!
The Garden, Pet Friendly | Terrace/patio

2. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (41 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is €167
includes taxes & fees
6 Oct - 7 Oct
Historic Tremain Cottages
Property grounds

3. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is €327
includes taxes & fees
11 Sept - 12 Sept
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Exterior detail

4. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is €155
includes taxes & fees
13 Sept - 14 Sept
Downtown Cottage
Exterior

5. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (66 reviews)
"The place was beautiful, cozy and so clean!!!! loved the pool and enjoyed spending my birthday there! will visit again soon!"
United States
Sara L.
The price is €206
includes taxes & fees
11 Sept - 12 Sept
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Property grounds

6. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (25 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is €258
includes taxes & fees
13 Sept - 14 Sept
Cozy Lake Front Cottage
Terrace/patio

7. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is €195
includes taxes & fees
11 Sept - 12 Sept
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Exterior

8. The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (52 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is €289
includes taxes & fees
28 Sept - 29 Sept
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

9. Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is €719
includes taxes & fees
21 Sept - 22 Sept
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Property grounds

10. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is €178
includes taxes & fees
14 Sept - 15 Sept
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Property grounds

11. Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (22 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is €222
includes taxes & fees
13 Sept - 14 Sept
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Interior

12. Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (17 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is €181
includes taxes & fees
14 Sept - 15 Sept
Beautiful Historic Cottage, Rendezvous
House (2 Bedrooms) | Interior

13. Mount Dora Home: Private Pool, Spa & Tropical Bar!

Mount Dora Home: Private Pool, Spa & Tropical Bar!
3.0 star property
Mount Dora
6.0 out of 10, (1 review)
The price is €293
includes taxes & fees
21 Sept - 22 Sept
Mount Dora Home: Private Pool, Spa & Tropical Bar!
Front of property

14. Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is €203
includes taxes & fees
24 Sept - 25 Sept
Mount Dora Cottages
Terrace/patio

15. Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"It was a perfect house for our short stay. Great location."
United States
Connie D.
The price is €191
includes taxes & fees
14 Sept - 15 Sept
Beautiful Historic Cottage, The Garden
House (4 Bedrooms) | Interior

16. Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is €290
includes taxes & fees
30 Sept - 1 Oct
Family Resort Home w Pool, BBQ & Game Room
Exterior

17. Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
6.8 out of 10, (3 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is €138
includes taxes & fees
11 Sept - 12 Sept
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Property grounds

18. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is €402
includes taxes & fees
17 Sept - 18 Sept
Th20 - 3BR House With Resort Access Near Parks
Exterior

19. Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (5 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is €187
includes taxes & fees
15 Sept - 16 Sept
Charming Historic Cottage with Cozy Porch and Garden Retreat
House (4 Bedrooms) | Floor plan

20. Family 4BR Home w/ Resort Pool Near Disney

Family 4BR Home w/ Resort Pool Near Disney
3.0 star property
Regal Palms
The price is €280
includes taxes & fees
5 Oct - 6 Oct
Family 4BR Home w/ Resort Pool Near Disney
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Beautiful"
Paris Deshun 3-night trip
Posted 1 hour ago
Universal's Cabana Bay Beach Resort

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
476
Accommodation
2643 Cottages
Lowest Price
€138
Highest Price
€719

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between €138 and €719 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.